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研究论文

二苯基八氢吲哚醇硅醚催化ɑ,β-不饱和醛不对称[3+3]氮杂环化反应合成苯并呋喃衍生物

温慧玲, 罗年华, 欧阳露, 罗人仕   

  1. 赣南医学院 赣州 341000
  • 收稿日期:2020-06-19 修回日期:2020-08-09 出版日期:2030-01-01 发布日期:2020-08-27
  • 通讯作者: 罗人仕 E-mail:luorenshi2010@163.com
  • 基金资助:
    国家自然科学基金(No.21962004,21562004),江西省自然科学基金(20192BAB203004),江西省教育厅项目(GJJ190829)及赣南医学院(QD201832,QD201816,YJ202027)资助项目.

Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric[3+3] Aza-Cyclization of ɑ, β-Unsaturated Aldehydes

HuiLing Wen, NianHua Luo, Lu Ouyang and RenShi Luo   

  1. Gannan Medical University, Ganzhou, 341000, Jiangxi Province, P. R. China
  • Received:2020-06-19 Revised:2020-08-09 Online:2030-01-01 Published:2020-08-27
  • Supported by:
    Project supported by the the National Natural Science Foundation of China (21962004, 21562004), Jiangxi provincial department of science and technology (20192BAB203004); Jiangxi Education Hall Science and Technology Foundation (GJJ190829) and Gannan Medical University (QD201832, QD201816,YJ202027).

二苯基八氢吲哚醇硅醚可高对映选择性催化3-氨基苯并呋喃与ɑβ-不饱和醛的[3+3]氮杂环化反应,获得高收率(高达93%)、高非对映选择性(dr>20:1)及高对映选择性(86%~>99%ee)的苯并呋喃衍生物。该方法还可获得克级规模的苯并呋喃衍生物。

关键词: 二苯基八氢吲哚醇硅醚, [3+3]氮杂环化, ɑ,β-不饱和醛, 3-氨基苯并呋喃

A highly enantioselective[3+3] aza-cyclization of ɑ, β-unsaturated aldehydes with 3-aminobenzofuran promoted by diphenylperhydroindolinol silyl ether has been describled, which affords benzofuran derivatives in high yields (up to 93%), diastereoselectivites (dr > 20:1) and enantioselectivities (86%~> 99% ee). This method also enables to obtain benzofuran derivative in gram scale-up.

Key words: diphenylperhydroindolinol silyl ether, [3+3]aza-cyclization, ɑ,β-unsaturated aldehydes, 3-Aminobenzofuran